EP1720881B8 - 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins - Google Patents

11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins Download PDF

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Publication number
EP1720881B8
EP1720881B8 EP05717846A EP05717846A EP1720881B8 EP 1720881 B8 EP1720881 B8 EP 1720881B8 EP 05717846 A EP05717846 A EP 05717846A EP 05717846 A EP05717846 A EP 05717846A EP 1720881 B8 EP1720881 B8 EP 1720881B8
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EP
European Patent Office
Prior art keywords
pyrrolobenzodiazepins
benzodiazepin
pyrrolo
hydroxy
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP05717846A
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German (de)
French (fr)
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EP1720881B9 (en
EP1720881A1 (en
EP1720881B1 (en
Inventor
Philip Wilson Howard
Stephen John Gregson
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Spirogen SARL
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Spirogen SARL
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Priority claimed from GB0404575A external-priority patent/GB0404575D0/en
Priority claimed from GB0426392A external-priority patent/GB0426392D0/en
Priority to PL10174003T priority Critical patent/PL2270010T3/en
Priority to SI200531679T priority patent/SI1720881T1/en
Application filed by Spirogen SARL filed Critical Spirogen SARL
Priority to EP10174003A priority patent/EP2270010B1/en
Priority to DK10174003.3T priority patent/DK2270010T3/en
Priority to PL05717846T priority patent/PL1720881T3/en
Publication of EP1720881A1 publication Critical patent/EP1720881A1/en
Publication of EP1720881B1 publication Critical patent/EP1720881B1/en
Application granted granted Critical
Publication of EP1720881B8 publication Critical patent/EP1720881B8/en
Priority to CY20131100152T priority patent/CY1113782T1/en
Publication of EP1720881B9 publication Critical patent/EP1720881B9/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Cardiology (AREA)
  • Rheumatology (AREA)
  • Vascular Medicine (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biomedical Technology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Compounds and method of synthesis of compounds of formula III: and salts, solvates and chemically protected forms thereof, wherein: R 15 is optionally substituted C 1-12 alkyl; R 10 and R 16 together form a double bond between N10 and C11, or R 10 is H and R 16 is OH; R 7 is independently selected from H, R, OH, OR, SH, SR, NH 2 , NHR, NRR', nitro, Me 3 Sn and halo, and the compound is a dimer with each monomer being of formula (III), where the R 8 groups of each monomers form together a dimer bridge.
EP05717846.9A 2004-03-01 2005-03-01 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins Active EP1720881B9 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
SI200531679T SI1720881T1 (en) 2004-03-01 2005-03-01 11-hydroxy-5h-pyrrolos2,1-ccs1,4cbenzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins
PL05717846T PL1720881T3 (en) 2004-03-01 2005-03-01 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins
PL10174003T PL2270010T3 (en) 2004-03-01 2005-03-01 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins
EP10174003A EP2270010B1 (en) 2004-03-01 2005-03-01 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins
DK10174003.3T DK2270010T3 (en) 2004-03-01 2005-03-01 11-Hydroxy-5h-pyrrolo [2,1-c] [1,4] benzodiazepin-5-one derivatives as important intermediates in the preparation of c2-substituted pyrrolobenzodiazepines
CY20131100152T CY1113782T1 (en) 2004-03-01 2013-02-19 11-Hydroxy-5H-pyrrolo [2,1-C] [1,4] benzodiazepine-5-one derivative as an intermediate key for the production of C2 substituted pyrrolidone

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0404575A GB0404575D0 (en) 2004-03-01 2004-03-01 Pyrrolobenzodiazepines
GB0426392A GB0426392D0 (en) 2004-12-01 2004-12-01 Pyrrolobenzodiazepines
PCT/GB2005/000768 WO2005085251A1 (en) 2004-03-01 2005-03-01 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepines

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP10174003.3 Division-Into 2010-08-25

Publications (4)

Publication Number Publication Date
EP1720881A1 EP1720881A1 (en) 2006-11-15
EP1720881B1 EP1720881B1 (en) 2012-12-12
EP1720881B8 true EP1720881B8 (en) 2013-01-16
EP1720881B9 EP1720881B9 (en) 2013-04-17

Family

ID=34921487

Family Applications (2)

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EP10174003A Active EP2270010B1 (en) 2004-03-01 2005-03-01 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins
EP05717846.9A Active EP1720881B9 (en) 2004-03-01 2005-03-01 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP10174003A Active EP2270010B1 (en) 2004-03-01 2005-03-01 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepins

Country Status (13)

Country Link
US (1) US7741319B2 (en)
EP (2) EP2270010B1 (en)
JP (2) JP4909258B2 (en)
AT (1) ATE542821T1 (en)
AU (1) AU2005219626B2 (en)
CA (1) CA2558195C (en)
CY (2) CY1112541T1 (en)
DK (2) DK1720881T3 (en)
ES (2) ES2398975T3 (en)
PL (2) PL1720881T3 (en)
PT (2) PT2270010E (en)
SI (2) SI1720881T1 (en)
WO (1) WO2005085251A1 (en)

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